Potassium Carbonate → N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-(2-hydroxyethoxy)ethoxy)-5-methylbenzamide

HRID 1890137

Reaktionsgleichung

Reaktionsgleichung von HRID 1890137
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[OH:28])[CH2:7][CH2:6]2.Cl[CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36])[CH2:7][CH2:6]2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 16738306N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-hydroxy-5-methylbenzamide

Produkt 1

HCID 68008900N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-(2-hydroxyethoxy)ethoxy)-5-methylbenzamideAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The mixture of 4a (0.65 g, 1.6 mmol), 2-(2-chloroethoxy)ethanol (0.64 g, 5.1 mmol), potassium carbonate (0.71 g, 5.1 mmol) in of N,N-Dimethylformamide (DMF) (25 mL) was refluxed over night under an atmosphere of nitrogrn. The reaction mixture was cooled to room temperature and quenched with 100 mL water. The aqueous solution was extracted with ethyl acetate (3 X2 50 mL). The combined organic layer was washed with brine (3×30 mL) and dried over Na2SO4. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography with methanol/dichloromethane (10/90, v/v) as the mobile phase to afford compound 5a (0.41 g; 51% yield) as a viscous yellow oil. 1H NMR (300 MHz, CDCl3): 1.68-1.79 (m, 4H), 2.31 (s, 3H), 2.50-2.60 (m, 2H), 2.72-2.76 (m, 2H), 2.82-2.85 (m, 2H), 3.46-3.60 (m, 8H), 3.80-3.90 (m, 8H), 4.18-4.24 (m, 2H), 6.49 (s, 1H), 6.58 (s, 1H), 6.79-6.83 (d, 1H), 7.16-7.24 (m, 1H), 7.98-7.80 (m, 1H), 8.18-8.26 (s, 1H).

Aufarbeitung

  1. temperaturewas refluxed over night under an atmosphere of nitrogrn
  2. customquenched with 100 mL water
  3. extractionThe aqueous solution was extracted with ethyl acetate (3 X2 50 mL)
  4. washThe combined organic layer was washed with brine (3×30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrating under reduced pressure
  7. customthe residue was purified by silica gel column chromatography with methanol/dichloromethane (10/90

Quellen und Nachweise

ORD-Eintrag
ord-15c68c1c5c5e4195b30dcf7e0b2b75d2
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08506927B2

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